Ethylene Glycol → 2-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenyl)-1,3-dioxolane

HRID 232421Notes

Reaction equation

HRID 232421 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:9]2)=[CH:4][CH:3]=1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:17]4[O:24][CH2:23][CH2:22][O:18]4)[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 533948533-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehyde

Product 1

HCID 536853242-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(2-(7-chloroquinolin-2-yl)ethenyl)benzaldehyde (step 1) (938 mg, 3.19 mmoles), ethylene glycol (200 μL, 1.15 equiv.), p-toluene-sulfonic acid (296 mg, 0.5 equiv.) and toluene (1.5 mL) was heated at reflux overnight. 25% aqueous NH4OAc was then added and the mixture extracted with EtOAc. Flash chromatography of the residue on silica with EtOAc:hexane 20:80 afforded the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe mixture extracted with EtOAc

Sources & evidence

ORD record
ord-2a38bd5e4fcc4dc08736d64062746eea
Source dataset
uspto-grants-1989_07
Patent number
US04851409

Reaction notes

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